


Date Night

by foreverwayward



Series: Date Night [1]
Category: SPN, Supernatural
Genre: Angst, Emotionally Hurt Dean Winchester, F/M, Fluff, Hurt Dean Winchester, Love, Reader-Insert
Language: English
Status: Completed
Published: 2020-02-10
Updated: 2020-02-10
Packaged: 2021-02-27 22:41:30
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,171
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22643536
Author URL: https://archiveofourown.org/users/foreverwayward/pseuds/foreverwayward
Summary: A nervous reader finds comfort in Dean.
Relationships: Dean Winchester/Reader, Dean Winchester/You
Series: Date Night [1]
Series URL: https://archiveofourown.org/series/1628854
Kudos: 21





	1. Chapter 1

You were so nervous you felt like your stomach was doing somersaults. You’re a friggin hunter for God’s sake. Your days consisted of killing vampires, werewolves, ghosts and all kinds of things that go bump in the night. But the idea of a date? It scared you senseless.

This had to go well. You were crazy about this guy for almost a year now and you were finally going out together. A _real_ date. Hunters don’t do that. Maybe that’s why you’re so unprepared.

As you walked down the bunker hallway, you tripped a little as you put on your second heel mid-walk. Standing up, you straightened your mid-thigh length cocktail dress and fluffed your hair. “Ok,” you whispered taking a deep breath. “You can do this.”

You walked into the library as a tall man stood with his back towards you. The heels beneath you clicked on the wooden floors and he turned to face you. It was Dean Winchester. His eyes seemed to lock on you but somehow you failed to notice.

Whether you were all cleaned up or in jeans and leather on a hunt, you were always perfect to him. But that night? He could have sworn his heart stopped when you walked in.

“So?” You asked. “How do I look?”

Dean swallowed hard as he was overwhelmed by his feelings for you. He couldn’t believe how beautiful you were. Clearing his throat, he finally answered in a husky voice, “I mean—wow. You, uh—you look amazing.” He smiled and his hands ran down his pants as almost to wipe off sweat from his nerves.

You sighed. “Oh thank god. I never wear this kinda thing and I thought I looked like an idiot,” you admitted chuckling.

“What? No. God no. You—you look incredible, Y/N.” Dean felt you take his breath away the closer you walked to him.

Putting your clutch on the table you pushed back your hair. “Then why am I so nervous?”

He couldn’t understand. How could someone so perfect not know she was? And yet, it was one of the things he loved most about you. “Well, you shouldn’t be.”

“I just don’t wanna screw this up, you know?”

“Yeah. I get that. But…I don’t think you know how amazing you are.”

You laughed and blushed. “Dean, stop.”

“I’m serious,” he said adamantly. His eyes locked into yours and he felt himself get lost. “Y/N, you have no idea how much the room lights up when you walk in. Or how infectious your laugh is. Or what a badass you are,” he chuckled in the back of his throat. “If there’s ever anyone that can’t see that? Then they don’t deserve you.”

“How do you always know just what to say?” You smiled up at him. Taking a deep breath, you grabbed your clutch. “Thank you, Dean. I feel a lot better now.” Getting on your tiptoes you kiss his cheek. “You’re the best.” Scurrying across the floor you headed towards the stairs to leave. “Alright, well I better get going. Don’t wanna keep him waiting too long. Thank you, Dean! I’ll be back late so don’t wait up! Love ya!”

Dean watched your every move as you finally closed the door behind you. He closed his eyes and breathed through the sharp pain in his chest knowing you would be out with someone else. But Dean knew he could never tell you how he felt. He thought he would never be good enough for you. You deserved more.

He stood where you had left him and put a hand on the table to support himself as he looked down. “…I love you, too,” he admitted to himself.


	2. Chapter 2

Y/N couldn’t have been out the door for more than two minutes and everything inside Dean was screaming for her. He didn’t want to go against everything he was feeling, but he was drowning in his love for her. The image of her in another man’s arms or someone else getting lost in her beautiful Y/E/C was enough to turn Dean ’s stomach. The hunter hated that he had been in love with her for so long and never told her. He felt like a coward, but he knew he could never be what Y/N deserved. She needed someone who wasn’t so broken; someone who wasn’t a hunter with so much baggage. She deserved a life with someone that could give her more. And that wasn’t him. **  
**

Dean looked up to the front door and took an eager step forward toward her. He growled under his breath with a scoff at himself as he forced his feet to stay planted. “ _Dammit_ ,” he muttered deeply into the silence before he ran up the metal stairs. The hunter’s boots clanked on the steps as he made his way up, his eyes never leaving the door.

He threw the door open and looked out to see her sitting in her car fixing her lipstick. Dean’s breath hitched realizing he was about to take the biggest leap he ever had. Taking long and purposeful steps, Dean tried to calm his breathing as he headed to her car. He tapped on the window and she jumped at the sound.

Y/N opened the door and looked up at him curiously. “Dean…?”

“Can you–can you please get out of the car?” He watched as her leg swung out of the car and her heel hit the ground. There wasn’t a single part of her Dean didn’t constantly study.

“What’s going on?”

Dean grunted under his breath with frustration for himself. “I’m not good at this crap.”

Y/N chuckled. “Not good at what? What are you talking about?”

“I–” Dean ran a hand down his face nervously. “I–you–you can’t go.”

“What are you talking about?”

“Don’t go. Don’t go out with him. …please?” Dean stumbled over his words as a lump grew in his throat. “Please, just don’t go.”

Her face scrunched as she focused on his anxious face. “Why? Dean, you’re being so weird.”

Awkwardly, he laughed and looked down at his feet feeling like a ridiculous teenager. “So I’m not just not good at this. I suck.” Stopping his nervous laughter, he cleared his throat. “Y/N…the thought of you with someone–with someone else…it’s like a knife in my gut.” He stepped closer to her as his entire existence ached for her. “I know, I know I don’t deserve you. But…” Dean’s voice almost broke as it went to a near whisper. “I’m so in love with you, Y/N. I have been for longer than I can remember. And I know, I have piss poor timing and take forever to say what I mean. But I need you, more than I’ve ever needed anything.” Dean smiled nervously as he looked into her eyes. Y/N’s eyes widened as she stared back at him without words. There was a silence and Dean felt his heart fall. “Please–please say something.”

Y/N scoffed under her breath with shock and she shook herself back to reality. “Dean, I–” He hung on her every word just praying he hadn’t ruined everything. “I have to go.”

She turned to get in her car and Dean’s hand immediately reached to hold Y/N’s wrist and she looked back at him. “No, please. Stay with me…”

“I can’t do this.” Y/N got into her car and quickly started the engine.

Dean went to her window and looked at her with a broken heart. “Y/N…” he practically pleaded as she put the car into drive. The hunter watched as she quickly drove out of sight and down the road. His hands went up onto his head and stayed there as his eyes welled until he pulled them forward, hard. All that remained was the dirt that had kicked out from under her tires floating in the breeze. It was over; she was gone. A tear ran down his cheek as he stood where she had left him. 

* * *

Dean sighed heavily as he sat on his bed against his headboard. His earphones were on as he tried to focus on the music rather than her face. The Winchester couldn’t focus with his mind reeling over what had happened only two hours before.

His eyes closed and his brow creased. Dean hated that he had been in love with her for so long and never told her until that night. Even worse, he’d made a fool of himself and maybe ruined everything between them.

There was a clacking in the hallway that got louder as it got closer. Dean couldn’t hear it with the music that played until his bedroom door swung open. There stood Y/N with her heels in her hand. She looked hurt, almost angry.

“You’re, uh–you’re back early,” he told her nervously. Dean knew that the date probably hadn’t gone well and he hated that she looked so flustered. But the selfish side of him was just glad she was home and not with the other guy.

“Yeah, I am,” Y/N bit. “Wasn’t like I could actually go on a date with what you said to me before I left.” Hesitantly, Dean slowly got off the bed to stand. His eyes were locked on her as he waited to see what she would do next. “You know? You had no right telling me you were in love with me.”

Taken back, Dean asked, “what?”

“I was fine. I was good. I was going on a date with a nice guy that I had liked for a long time now. Someone I thought I could really have something with. But I had feelings for you for years, Dean. _Years_. And did you ever do anything? No. You waited until I tried to move on and then pulled this crap.”

Dean was shocked at what she said but then grew frustrated. “You think I _want_ to feel this way? You think I _want_ to think of you every second of every day? Do you have any idea how hard it was to tell you all that? And if you had feelings for me, why didn’t _you_ say anything?”

“Because all you did was hook up with random women. You always would talk about how hunters don’t get to have the normal things in life and that relationships or feelings just get in the way. That they’re dangerous. How _could_ I tell you?” Y/N huffed before she turned to leave down the hall.

“Wait a minute!” Dean shouted out before chasing after her. “We’re not done.”

Condescendingly, she chuckled softly. “Oh, yes we are. I can not believe you, Dean Winchester.”

He ran to her and grabbed her wrist again, only a little firmer that time. Y/N spun around to look at him and his chest was rising and falling quickly with nerves as hers did the same. “You’re right. Okay? I did and said all of that. But I was…” Dean stopped and tried to figure out what to say. “I was an ass, okay?”

“And that’s just supposed to make it all okay now?”

“No! I know it doesn’t. But I also know that you and me? _We_ work,” he told her sternly. “With all the crap in our lives, we’re the only thing that makes sense. And I may be stupid, but I’m not about to just let that go. Look at me–look at me and tell me you don’t feel the same way.”

“Dean…”

Before she could finish her sentence, Dean’s hands took the side of her face and he scrunched his eyes shut with passion as he kissed her deeply. Years of longing and love pouring from him as he felt her lips for the first time. He had to control the moan that grew in his chest at the impact.

Y/N froze for a second and then pushed him away. Dean looked at her with his eyes locked on hers. She met his gaze and nearly gasped as she dropped her shoes and threw her arms around his neck. Y/N let go and kissed him with everything she had.

Something in Dean melted and he held her tightly against him as they shared their feelings without words. That kiss spoke more feelings than anything they would say to each other. Finally, they pulled away as Y/N tried to take a step back and her eyes met his once again. “If we do this, Dean…this is for real. I won’t be another notch on your belt.”

Kissing her once again, he inhaled deeply with his lips against hers. He gently stopped and cupped her cheek in his hand as his thumb brushed her face softly. “This is as real as it gets, Y/N.” Dean’s forehead leaned against hers and they closed their eyes with their arms wrapped around each other. “It’s you and me.”


End file.
